Sodium hydride → HCID 67477363, compound

Participants

Reaction Steps

The reaction was carried out under argon. The diastereomer mixture of (RS,4S)-4-[4-cyano-2-(methylsulfinyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile and (SS,4S)-4-[4-cyano-2-(methylsulfinyl)phenyl]-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (444.4 mg, 1000 μmol) was initially charged in THF (10 ml), and sodium hydride (60% in mineral oil; 56 mg, 1400 μmol) was added at 0° C. The mixture was warmed to RT and stirred for 20 min. A solution of methanesulfonyl chloride (160.4 mg, 1400 μmol; 1.4 eq.) in THF (5 ml) was then slowly added dropwise. After a reaction time of 16 h, more methanesulfonyl chloride (54 mg, 467 μmol; 0.47 eq.) was added and the mixture was stirred at RT for another 60 min. Saturated ammonium chloride solution (50 ml) was added, and the reaction mixture then extracted with ethyl acetate (3×30 ml). The combined organic phases were dried over solid sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by preparative HPLC (column: Gromsil C-18 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→80:20). This gave the title compound as a colorless solid (245 mg, 47% of theory).

Provenance & Evidence